(UPDATED For 2024!) 9 Easy Ways To Style Wide Leg High Waisted Jeans For Every Season

Updated October 2024

Back in my day, they called them “hip-huggers”, but I digress! Wide leg high waisted jeans are back and trending this season, so I’m sharing nine perfect, easy-to-put-together outfits featuring your new fave! If you don’t own a pair yet, don’t worry! I’ve also included the best options (curve-friendly!) for your style and budget.

Want a full review of the cargo jeans featured in this post? Check out my latest post styling wide leg cargo jeans for Summer!

If you’re worried about going full 90s throwback, I totally get it. But, this season’s iteration of wide leg jeans come in a tapered, figure-flattering fit and tons of different washes and colors (no acid wash, so far!). They definitely don’t “hang” off of you like their predecessors and they pair just as well with a fun tee as they do with a sexy bodysuit and heels.

DISCLOSURE: I only recommend products I would use myself and all opinions expressed here are our own. This post contains affiliate links from which I earn a commission, at no extra cost to you, when you make a purchase. Read more about it HERE.

The Best Wide Leg High Waisted Jeans

The first pair I’m wearing is from Femi Boutique, a Black-owned boutique I recently discovered online, and they’re sooo soft! No gaps around my waist and they’re *just* long enough to wear with booties or heels (I’m 5’4 & a size 14 for reference). They’re sold out in a few sizes, so if your size is gone, check out the list below to find your fave.

The second pair I’m wearing are a lightweight “Dreamy Drape” denim from American Eagle. You can read my full review here on these high waist wide leg cargo jeans, but I’ll say very quickly: they’re comfortable, truly lightweight, and incredibly flattering.

Don’t miss out in your FREE Timeless Wardrobe Essentials Guide with styling tips, outfit ideas, and 15 timeless, year-round style essentials

The Trick To Buying Jeans Online

I usually prefer to buy my denim in person so I can feel it out, try it on, etc. But we don’t have a ton of shopping options that are close to us, so I have also purchased my fair share of jeans online. Here are my tried-and-true tricks for buying denim online.

• TAKE YOUR MEASUREMENTS: Make sure to take waist & hip measurements so you have something to compare to the chart online. It’s a pain, but so helpful in the long run!

• KNOW YOUR RISE: If you can, head to the store to try on a few different rise levels and figure out what suits you best. I can typically go with a mid-rise or normal high-rise. I never do the popular “super high waist” styles because they tend to sit right under my boobs, since I’m only 5’4. Not very flattering!

• WHAT’S THE FABRIC CONTENT: Check out the Elastane or Spandex content (both materials will add stretch). Do you like a tighter, more uniform fit? Go with low to no spandex.

• CHECK OUT THE MODEL: Old Navy & Madewell have really stepped it up lately in this department. You can select the size that matches yours and their sites will show you what the jeans look like on that body type. Super helpful when you can’t try it on yourself.

• READ THOSE REVIEWS: Nowadays, most stores will let you attach a pic to your review which is incredibly helpful and can give you a better idea of how a pair of jeans will match up to your body type.

How To Wear Wide Leg Jeans

As you’ll see in a second, you can style wide leg high waisted jeans just you like you would any other kind of jean. A few things to keep in mind: go easy on the oversized tops and sweaters. The wide legs already add a fair amount of volume and pairing with an oversized top may be too much.

Don’t be afraid to play with hemlines! Mine have a raw edge which I thought was fun. There are also wide leg jeans that are cropped and provide the perfect opportunity to show off a those new booties. Considering rocking this trend to the office? Consider these Wide Leg Tailored Pants. They’re on-trend and perfectly office-appropriate.

By the way, if you enjoyed this post, you may want to check out my list of over 120 Black-Owned Online Boutiques. With styles from boho to classic to trendy and a full range of sizes, there’s something for everyone on this list!

6 Wide Leg High Waisted Jean Outfits For Every Season

Fall

I feel like Boho was really big in home decor last year and, this season, it’s sort of spilled over into our clothing choices. Whether you add little bohemian touches, like this long-line cardi, or go full out Boho Goddess, it’s definitely a trend to try out! This amazing cardigan from Modern Gypsy is all sold out, but I linked similar options below!

SHOP THE LOOK

Spring/ Fall

One of my fave ways to wear these jeans. Avoid the “denim tuxedo” look by switching up the wash. Here, I went for the darker wash on top.

SHOP THE LOOK

SHOP THE LOOK

Fall/ Winter

I mean, the Pumpkin Patch is a double-whammy: great photo-ops and the kids always have a blast! These insane earrings from TelJae are sold out, but she’s got other beautiful options still in stock! This sweater is also sold out, but I found a really impressive dupe; keep scrolling to check it out!

SHOP THE LOOK

Winter

This look is super versatile; you could do brunch or date night with your partner depending on the shoes!

SHOP THE LOOK

Winter

This shacket is fairly lightweight, but layered over a chunky sweater, definitely provides warmth!

Summer

Can you wear wide leg high waisted jeans in the Summer time? Of course you can! The trick is to find a great lightweight pair like these that are breathable and still comfy in the Summer heat.

SHOP THE LOOK

Spring

I love pairing high waisted wide leg jeans with a simple, elevated basic like this soft, linen blend top! Blazer on for an extra layer in Spring, skip the blazer for Summer.

GET THE LOOK

Feeling inspired, but not sure where to start? Read up on my best tips on how to look put together every single day.

Summer

An unexpected pairing: these super casual cargo jeans with this sweet and romantic eyelet top. I added tennis shoes to keep the whole outfit from being too “girly” but a sandal would also work for a different vibe!

GET THE LOOK

Spring

They’re a necessity, so you might as well look cute while running them! HINT: If your pants, like mine, are a tad too long to wear with sneakers, cuff them to the desired length, spray the bottom with a bit of spray starch and iron them. That should hold your hemline throughout the day(:

SHOP THE LOOK

How are you wearing your favorite wide leg high waisted jeans this season? Share pics below or tag me on Instagram!

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